The total synthesis of antibiotics, fomannosin and frenolicin, is proposed. In both cases, new methodology is being developed as a primary goal. For fomannosin, the Diels-Alder reaction of cyclobutene derivatives is being studied as a means to assemble the skeleton and control stereochemistry. A second approach will rely on a ketene/alkene cycloaddition to control the stereochemistry. New methods of aromatic ring manipulation involving transition metal pi-complexes are being developed for naphthalene and anthracene quinone synthesis. Using these methods, we will pursue the synthesis of an epoxynaphthoquinone, frenolicin. Additional general new techniques for organic natural product synthesis will focus on low valent nickel intermediates and flourophosphine ligands. The goal is a general coupling reaction of organic halides with nucleophilic carbon, oxygen, and nitrogen.